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“Irony Doesn’t Scale”

Assessing the health of our system

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Last week, my co-founder Rich Ziade wrote about what he’s learned and experienced over the last two years of running our product studio, Postlight. Which made me wonder: What have I learned working alongside him?

J.H. van den Broek, Competition Design for Affordable Workers’ Dwellings, ‘Optimum’, 1934

Before Postlight I’d never co-founded anything. I’d been a consultant, editor, writer, product lead, programmer, advisor, team builder, facilitator, and teacher, but not a leader. Suddenly I was a co-founder of a surprisingly large product shop. Soon after we launched, as Rich described, the relationships we were counting on turned to dust.

In October 2015 we were an agency with nearly 30 employees, but with no clients. In October 2017 we have many clients, we are growing steadily, the brand is good, and the company is exceptionally steady. It was a challenge.


There’s a piece of writing I like. It was originally posted on LiveJournal and it’s called “How to Keep Someone With You Forever.”

It’s a recipe for building a “sick system.” It tells you exactly how to create a screwed up environment driven by panic and powered by manipulation.

Keep everything on the edge. Make sure there’s never quite enough money, or time, or goods, or status, or anything else people might want. Insufficiency makes sick systems self-perpetuating, because if there’s never enough — to fix the system, and never enough time to think of a better solution, everyone has to work on all six cylinders just to keep the system from collapsing.

A lot of businesses, especially agencies, are sick systems. They make a cult of their “visionary” founders. And they keep going but never seem to thrive — they always need just one more lucky break before things improve. Payments are late. Projects are late. The phone rings all weekend. That’s not what we wanted to build. We wanted to thrive. I made a list:


Characteristics of a Well System

  • Hire people who like to work hard and who have something to prove.
  • Encourage people to own and manage large blocks of their own time, and give people time to think and make thinking part of the job—not extra.
  • Let people rest. Encourage them to go home at sensible times. If they work late give them time off to make up for it.
  • Aim for consistency. Set emotional boundaries and expectations, be clear about rewards, and protect people where possible from crises so they can plan their time.
  • Make their success their own and credit them for it.
  • Don’t promise happiness. Promise fair pay and good work.

But How Does it Work in Theory?

When we were a year old we collectively drafted a statement of values, which carries a lot of the same intent as that list above—and later we prefaced that statement of values with a clear, simple mission.

Do we live it? We definitely try! Then again, you could point to anything in our mission statement and say: “Yeah, right, but what about when…

Here’s the most difficult thing in co-founderhood: There is no true metric of success, not even profits. When I was a writer and a piece was published I could see the tweets, and sometimes the traffic metrics. I could see who emailed me. And then I’d chase the next success, often for months.

For a long time at Postlight, I kept looking around for signs like that. They never came. Eventually I realized that success is not about big hits. It’s actually in the opportunity to improve. How could our sales pipeline be better-managed? How could our team be coached on client interaction? Who seems frustrated, who could use coffee, who should be pinged on Slack? How could our meetings be more efficient, and in lesser quantities? Do we need more plants?

Being in the position to address those questions is success. Having choices, optionality, and the ability to adapt — is success.

Less metaphysically, the office is tidy and well-lit (and remote employees are well-supported, too), our books are in order, and the overall environment is respectful. The work, which I love, is excellent—we’re building attractive, complex apps with thousands of components, for media, finance, and for NGOs. That’s what we’re built to do.

No matter what I’ve screwed up, or what opportunities we might have missed, you cannot take away the fact of it: We ship, clients keep hiring us back, and our people go home at night. They have optionality in their lives, too, and they deserve to have it. All credit to the team.

That’s success.

The sunbonnet babies in Holland; a second reader

Quiet Alert

From working alongside our team, and especially Rich, I have developed new, practical skills. I can sell millions of dollars worth of services. I can estimate out a seven-figure product engagement, although I still need to talk through all the particulars. I can spot problems in process. Bully for me.

I’ve also become less open and vulnerable. For complicated reasons.

I used to put myself out there—more than most people. I wrote for magazines and on the web about my family’s issues with fertility, my struggle with my weight, and so forth. I wrote deeply personal essays and I gave readings in little theaters. This is unusual in a technology executive. And I was used to a certain ironic, self-deprecating, and intimate kind of conversation with my peers.

But when the boss is self-deprecating it becomes someone’s job to lift him up. If I talk or chat on Slack about a bad day, I’m de-facto asking someone to soothe me. Some topics are fine: Kids being annoying, not getting enough sleep. But people need to mind their work, not me. The social contract is not, “tend to Paul.” If people do that—sick system.

I’m not a robot by any means. But I’ve learned to watch what I say. If there’s one rule that applies everywhere, it’s that Irony Doesn’t Scale. Jokes and asides can be taken out of context; witty complaints can be read as lack of enthusiasm. People are watching closely for clues to their future. Your dry little bon mot can be read as “He’s joking but maybe we are doomed!” You are always just one hilarious joke away from a sick system.

Parents of newborns learn to look for (and enjoy) a state called “quiet alert,” when the baby is just resting there with eyes open, taking everything in. Sometimes when I’m running my mouth and making my weird jokes a voice in the back of my head sets off a siren and goes, “Quiet alert! Quiet alert!” That’s the ideal state of a manager.

Organizational diagram of the New York and Erie Railroad, 1855

Accepting Asymmetry

For a long time I wanted to pretend that everything could be flat and symmetrical and that everyone was an equal here, with equal voice. But flat organizations, like irony, don’t scale.

I am the co-founder. My word is co-law and what I say co-goes. I don’t like controlling people’s access to health care, but due to a series of bad laws, I do, and I co-inherit all of the ethical responsibilities of that. I also work to bring work into the company to pay the health insurance bill. That’s my task above all others. This has all been new for me.

Sometimes, in consultation with others here, I make decisions about other people’s lives. Hiring is particularly hard. We hire carefully. And knowing that smart, talented people will take the rejection personally no matter how formal and buttoned up our HR process is sucks. Layoffs are far more horrible and require months of planning and second-guessing—the asymmetry in the relationship is at its most bare. I don’t enjoy having power over other people, but I’m realizing that there’s a craft there too. And I learn from the people around me. Co-whatever-I-am aside, I am very lucky in my peers.

I try to ask myself these questions, over and over:

  • How will this decision affect not an individual employee, but their family? Because it will.
  • What would it be like to work for an individual employee?

Careers are long and things change. A junior engineer or senior product manager may one day be my boss.

That’s not purely hypothetical. One of our best client relationships is with a former student of mine. In a real way, that student now has power over us. I’m glad we built a polite and respectful relationship years ago, in a classroom.


Those are the things I’ve learned in two years. There are many other things left to learn, and many where I could have learned a little bit better. Doubtless some people wish I’d learned different lessons.

I’m still a reluctant capitalist but I’ve loved working with this team and absolutely enjoyed letting my raw hustle and ambition take over from my self-doubt and imposter syndrome. Seeing casual emails turn into big checks does wonders for a writer’s confidence; seeing those checks turn into working, good-looking, successful software does even more.

So: There have been many sites launched, platforms built, hires made, bills paid, podcasts recorded. I’m most proud of helping to build Postlight into a mostly-well system, where people can focus on their respective crafts, and where I can attend a product meeting and review the good work that people are doing, and offer the experience I have. Because I do love the work.

Quiet alert.


Oh and obviously, we’re hiring!

Story published on Oct 11, 2017.